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Synfacts 2007(1): 0015-0015  
DOI: 10.1055/s-2006-955646
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Tetronolide

Contributor(s): Philip Kocienski
R. K. Boeckman, Jr.*, P. Shao, S. T. Wrobleski, D. J. Boehmler, G. R. Heintzelman, A. J. Barbosa
University of Rochester, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Tetronolide is the aglycone of tetrocarcin A, a compound which selectively inhibits the mitochondrial functions of the Bcl-2 family of proteins that serve as apoptosis inhibitors. The synthesis depicted twice uses Diels-Alder reactions to create three of the five rings. A new camphor-derived chiral auxiliary (see structure E) makes its debut. See also: R. K. Boeckman, J. E. Pero, D. J. Boehmler J. Am. Chem. Soc. 2006, 128, 11032-11033.